AU2007263828B2 - Diketopyrrolopyrrole polymers as organic semiconductors - Google Patents
Diketopyrrolopyrrole polymers as organic semiconductors Download PDFInfo
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- AU2007263828B2 AU2007263828B2 AU2007263828A AU2007263828A AU2007263828B2 AU 2007263828 B2 AU2007263828 B2 AU 2007263828B2 AU 2007263828 A AU2007263828 A AU 2007263828A AU 2007263828 A AU2007263828 A AU 2007263828A AU 2007263828 B2 AU2007263828 B2 AU 2007263828B2
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- 229920000642 polymer Polymers 0.000 title claims abstract description 150
- 239000004065 semiconductor Substances 0.000 title claims abstract description 49
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title claims description 35
- 230000005669 field effect Effects 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- -1 cyano, phenyl Chemical group 0.000 claims description 139
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 239000000463 material Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000000243 solution Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- 239000000758 substrate Substances 0.000 claims description 37
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 33
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229910052786 argon Inorganic materials 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 17
- 239000010409 thin film Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 239000012212 insulator Substances 0.000 claims description 15
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000007704 transition Effects 0.000 claims description 10
- 229910052727 yttrium Inorganic materials 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000009499 grossing Methods 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000006414 CCl Chemical group ClC* 0.000 claims description 5
- 125000003172 aldehyde group Chemical group 0.000 claims description 5
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
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- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
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- 239000004020 conductor Substances 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005401 siloxanyl group Chemical group 0.000 claims description 3
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 16
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C—CHEMISTRY; METALLURGY
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| PCT/EP2007/056102 WO2008000664A1 (en) | 2006-06-30 | 2007-06-20 | Diketopyrrolopyrrole polymers as organic semiconductors |
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Families Citing this family (107)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7781673B2 (en) | 2005-07-14 | 2010-08-24 | Konarka Technologies, Inc. | Polymers with low band gaps and high charge mobility |
| US20070181179A1 (en) | 2005-12-21 | 2007-08-09 | Konarka Technologies, Inc. | Tandem photovoltaic cells |
| BRPI0713952A2 (pt) | 2006-06-30 | 2012-12-04 | Ciba Holding Inc | polìmeros de dicetopirrolopirrol como semicondutores orgánicos |
| US8008421B2 (en) | 2006-10-11 | 2011-08-30 | Konarka Technologies, Inc. | Photovoltaic cell with silole-containing polymer |
| US8008424B2 (en) | 2006-10-11 | 2011-08-30 | Konarka Technologies, Inc. | Photovoltaic cell with thiazole-containing polymer |
| US7910684B2 (en) | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
| US7932344B2 (en) * | 2007-09-06 | 2011-04-26 | Xerox Corporation | Diketopyrrolopyrrole-based polymers |
| KR101568436B1 (ko) * | 2007-10-25 | 2015-11-11 | 바스프 에스이 | 유기 반도체로서 케토피롤 |
| EP2114085A1 (en) * | 2008-04-28 | 2009-11-04 | Nederlandse Centrale Organisatie Voor Toegepast Natuurwetenschappelijk Onderzoek TNO | Composite microphone, microphone assembly and method of manufacturing those |
| KR101703034B1 (ko) | 2008-07-18 | 2017-02-06 | 유디씨 아일랜드 리미티드 | 전자 용품을 위한 아자피렌 |
| WO2010049323A1 (en) * | 2008-10-31 | 2010-05-06 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| US10224484B2 (en) | 2008-10-31 | 2019-03-05 | Basf Se | Diketopyrrolopyrrole polymers for use in organic field effect transistors |
| CN107099023B (zh) * | 2008-10-31 | 2019-10-22 | 巴斯夫欧洲公司 | 用于有机场效应晶体管的二酮吡咯并吡咯聚合物 |
| WO2010108873A1 (en) * | 2009-03-23 | 2010-09-30 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| US20100326525A1 (en) * | 2009-03-26 | 2010-12-30 | Thuc-Quyen Nguyen | Molecular semiconductors containing diketopyrrolopyrrole and dithioketopyrrolopyrrole chromophores for small molecule or vapor processed solar cells |
| JP5396128B2 (ja) * | 2009-03-31 | 2014-01-22 | 大阪瓦斯株式会社 | ジケトピロロピロール骨格を有するポリマーおよび白色発光材料 |
| US9067942B2 (en) * | 2009-04-08 | 2015-06-30 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use as semiconductors |
| EP2432817B1 (en) * | 2009-05-21 | 2015-02-11 | Raynergy Tek Inc. | Conjugated polymers and their use in optoelectronic devices |
| EP2435498A4 (en) * | 2009-05-26 | 2013-12-18 | Univ Florida | GREEN SOLUBLE CONJUGATED POLYMERS CHARACTERIZED BY GREAT MOBILITY OF LOAD CARRIERS |
| BRPI1011853A2 (pt) * | 2009-05-27 | 2019-09-24 | Basf Se | polímero, material, camada ou componente semicondutores orgânicos, dispositivo semicondutor, processos para a preparação de um dispositivo semicondutor orgânico, e de um polímero, e, uso do polímero e/ou do material, camada ou componente semicondutores orgãnicos. |
| DE112010002086B4 (de) * | 2009-05-27 | 2020-07-09 | Basf Se | Verfahren zum Polymerisieren von (hetero)aromatischen Verbindungen |
| WO2011002927A2 (en) | 2009-06-30 | 2011-01-06 | Plextronics, Inc. | Novel compositions, methods and polymers |
| US8624232B2 (en) | 2009-08-28 | 2014-01-07 | Prashant Sonar | Ambipolar polymeric semiconductor materials and organic electronic devices |
| KR101867784B1 (ko) | 2009-08-28 | 2018-06-15 | 에이전시 포 사이언스, 테크놀로지 앤드 리서치 | 폴리머 반도체, 소자 및 이를 제조하는 방법 |
| JP5685778B2 (ja) | 2009-09-04 | 2015-03-18 | ソルベイ ユーエスエイ インコーポレイテッド | 光電池およびジケトンベースのポリマーを含む、有機電子素子およびポリマー |
| JP5782703B2 (ja) * | 2009-10-29 | 2015-09-24 | 住友化学株式会社 | 高分子化合物及びそれを用いた電子素子 |
| WO2011119446A1 (en) * | 2010-03-20 | 2011-09-29 | Polyera Corporation | Pyrrolo[3,2-b]pyrrole semiconducting compounds and devices incorporating same |
| EP2560965B1 (en) | 2010-04-19 | 2017-06-14 | Merck Patent GmbH | Polymers of benzodithiophene and their use as organic semiconductors |
| WO2011144566A2 (en) * | 2010-05-19 | 2011-11-24 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| KR20130094773A (ko) | 2010-06-24 | 2013-08-26 | 바스프 에스이 | 온/오프 전류비가 개선되고 임계 이동이 제어가능한 유기 전계 효과 트랜지스터 |
| US20110315967A1 (en) * | 2010-06-24 | 2011-12-29 | Basf Se | Organic field effect transistor with improved current on/off ratio and controllable threshold shift |
| US9359505B2 (en) | 2010-07-27 | 2016-06-07 | Konica Minolta Holdings, Inc. | Gas barrier film, process for production of gas barrier film, and electronic device |
| WO2012017005A2 (en) | 2010-08-05 | 2012-02-09 | Basf Se | Polymers based on benzodiones |
| GB201013820D0 (en) * | 2010-08-18 | 2010-09-29 | Cambridge Display Tech Ltd | Low contact resistance organic thin film transistors |
| EP2610013A4 (en) | 2010-08-25 | 2016-12-21 | Konica Minolta Holdings Inc | METHOD FOR PRODUCING A GAS BRAKE PACK AND ORGANIC PHOTOELECTRIC CONVERTER ELEMENT |
| US20130200351A1 (en) * | 2010-09-10 | 2013-08-08 | Sumitomo Chemical Company, Limited | Polymer compound and organic photoelectric conversion device |
| US8946376B2 (en) | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
| WO2012050070A1 (ja) * | 2010-10-13 | 2012-04-19 | 住友化学株式会社 | 高分子化合物及びそれを用いた有機光電変換素子 |
| US9187600B2 (en) | 2010-11-01 | 2015-11-17 | Basf Se | Polyimides as dielectric |
| CN103189971B (zh) | 2010-11-01 | 2016-02-17 | 巴斯夫欧洲公司 | 作为电介质的聚酰亚胺 |
| WO2012060283A1 (ja) * | 2010-11-02 | 2012-05-10 | 住友化学株式会社 | 高分子化合物及びそれを用いた有機光電変換素子 |
| US8598450B2 (en) * | 2010-11-24 | 2013-12-03 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
| US20130228771A1 (en) | 2010-12-22 | 2013-09-05 | Basf Se | Semiconductor structure and method for its production |
| US9362524B2 (en) | 2010-12-27 | 2016-06-07 | Konica Minolta, Inc. | Method for producing gas barrier film, gas barrier film, and electronic device |
| EP2660041B1 (en) | 2010-12-27 | 2015-06-17 | Konica Minolta, Inc. | Gas-barrier film and electronic device |
| CN103415940A (zh) | 2011-03-11 | 2013-11-27 | 默克专利股份有限公司 | 共轭聚合物 |
| CN103443865A (zh) | 2011-03-25 | 2013-12-11 | 默克专利股份有限公司 | 吡咯并[3,2-b]吡咯-2,5-二酮和它们作为有机半导体的用途 |
| WO2012165128A1 (ja) * | 2011-05-27 | 2012-12-06 | 住友化学株式会社 | 高分子化合物及び有機光電変換素子 |
| US9074050B2 (en) | 2011-05-30 | 2015-07-07 | Basf Se | Process for the production of polymers by using coupling reactions |
| CN103619855B (zh) | 2011-06-22 | 2017-08-08 | 巴斯夫欧洲公司 | 用于有机半导体器件的二酮基吡咯并吡咯低聚物 |
| US9871216B2 (en) | 2011-08-09 | 2018-01-16 | Konica Minolta, Inc. | Organic photoelectric conversion element and organic solar cell using the same |
| JP2013055322A (ja) * | 2011-08-11 | 2013-03-21 | Mitsubishi Chemicals Corp | 光電変換素子、太陽電池及び太陽電池モジュール |
| TW201321427A (zh) | 2011-08-19 | 2013-06-01 | Univ Washington | 基於二酮吡咯並吡咯之新型聚（雜亞芳基亞乙烯基） |
| US9209412B2 (en) | 2011-09-02 | 2015-12-08 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
| KR20140101788A (ko) | 2011-11-15 | 2014-08-20 | 바스프 에스이 | 유기 반도체 소자 및 이의 제조 방법 |
| EP2783846A4 (en) | 2011-11-24 | 2015-09-02 | Konica Minolta Inc | GAS BARRIER LAYER AND ELECTRONIC DEVICE THEREFOR |
| US8598299B2 (en) * | 2011-12-06 | 2013-12-03 | Xerox Corporation | Semiconductor composition |
| WO2013083506A1 (en) | 2011-12-07 | 2013-06-13 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| CN103975453B (zh) | 2011-12-07 | 2018-01-30 | 巴斯夫欧洲公司 | 有机场效应晶体管 |
| JP5872872B2 (ja) * | 2011-12-12 | 2016-03-01 | Ｎｅｃトーキン株式会社 | 導電性高分子組成物の製造方法、導電性高分子材料の製造方法、導電性基材の製造方法、電極の製造方法および固体電解コンデンサの製造方法 |
| JP5952551B2 (ja) | 2011-12-12 | 2016-07-13 | Ｎｅｃトーキン株式会社 | 導電性高分子組成物およびその製造方法、導電性高分子材料の製造方法、導電性基材の製造方法、電極の製造方法、電子デバイスの製造方法並びに固体電解コンデンサの製造方法 |
| CN104185648A (zh) | 2012-04-02 | 2014-12-03 | 巴斯夫欧洲公司 | 用于电子应用的菲并[9,10-b]呋喃聚合物及小分子 |
| JP6395702B2 (ja) * | 2012-04-04 | 2018-09-26 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ジケトピロロピロールポリマーおよび小分子 |
| US9379335B2 (en) | 2012-04-08 | 2016-06-28 | The Regents Of The University Of California | Benzodipyrrolidones and their polymers: synthesis and applications for organic electronics and optoelectronics |
| EP2851192A4 (en) | 2012-05-14 | 2015-12-23 | Konica Minolta Inc | GASPERRFILM, METHOD FOR THE PRODUCTION OF GASPERRFILMS AND ELECTRONIC DEVICE |
| US20150144846A1 (en) * | 2012-06-04 | 2015-05-28 | Merck Patent Gmbh | Organic semiconductor |
| CN104470932A (zh) | 2012-07-23 | 2015-03-25 | 巴斯夫欧洲公司 | 用于电子应用的二噻吩并苯并呋喃聚合物和小分子 |
| WO2014031733A1 (en) * | 2012-08-22 | 2014-02-27 | University Of Washington Through Its Center For Commercialization | Diketopyrrolopyrrole polymers for electronics and optoelectronics |
| US9312044B2 (en) * | 2012-08-27 | 2016-04-12 | Corning Incoporated | Semiconducting fused thiophene polymer ink formulation |
| EP2928940B1 (en) | 2012-12-04 | 2021-03-03 | CLAP Co., Ltd. | Functionalized benzodithiophene polymers for electronic application |
| KR101589048B1 (ko) * | 2012-12-14 | 2016-01-27 | 경상대학교산학협력단 | 신규한 유기반도체 화합물 및 이를 포함하는 유기전자소자 |
| KR101514207B1 (ko) * | 2013-04-15 | 2015-06-05 | 한국과학기술연구원 | 낮은 밴드갭을 갖는 고분자 화합물, 이를 포함하는 유기태양전지 및 이의 제조방법 |
| WO2014180704A1 (en) | 2013-05-06 | 2014-11-13 | Basf Se | Soluble cyclic imides containing polymers as dielectrics in organic electronic applications |
| KR101485398B1 (ko) | 2013-05-07 | 2015-01-26 | 경상대학교산학협력단 | 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자 |
| EP3013906B1 (en) * | 2013-06-24 | 2020-03-25 | Basf Se | Polymers based on fused diketopyrrolopyrroles |
| EP2818493A1 (en) | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| KR101961985B1 (ko) | 2013-06-27 | 2019-03-25 | 바스프 에스이 | 유전체로서의 복분해 중합체 |
| KR101754044B1 (ko) | 2013-07-08 | 2017-07-04 | 바스프 에스이 | 아지드계 가교제 |
| US9761803B2 (en) | 2013-07-22 | 2017-09-12 | Xerox Corporation | Semiconductor composition |
| US10693080B2 (en) | 2013-11-21 | 2020-06-23 | Daicel Corporation | Solvent for producing organic transistor |
| JP6354157B2 (ja) * | 2013-12-26 | 2018-07-11 | 日立化成株式会社 | 電荷輸送性材料、該材料を用いたインク組成物、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、表示装置及び照明装置 |
| KR101630173B1 (ko) | 2014-01-17 | 2016-06-24 | 경상대학교산학협력단 | 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체 |
| KR101704110B1 (ko) * | 2014-01-17 | 2017-02-07 | 주식회사 엘지화학 | 신규한 화합물 및 이를 포함하는 유기 태양 전지 |
| US9399698B2 (en) | 2014-01-31 | 2016-07-26 | Xerox Corporation | Processes for purifying diketopyrrolopyrrole copolymers |
| KR101513883B1 (ko) * | 2014-02-07 | 2015-04-21 | 경상대학교산학협력단 | 신규한 중합체 및 이를 포함하는 유기전자소자 |
| KR101600031B1 (ko) | 2014-03-24 | 2016-03-07 | 경상대학교산학협력단 | 비대칭 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자 |
| KR102143429B1 (ko) | 2014-03-25 | 2020-08-11 | 경상대학교산학협력단 | 다이케토피롤로피롤 중합체 및 이를 채용하고 있는 유기 전자 소자 |
| KR102099612B1 (ko) | 2014-03-27 | 2020-04-10 | 경상대학교산학협력단 | 다이케토피롤로피롤 중합체 및 이를 채용하고 있는 유기 전자 소자 |
| WO2016046659A1 (en) | 2014-09-25 | 2016-03-31 | Basf Se | Ether-based polymers as photo-crosslinkable dielectrics |
| CN104774318B (zh) * | 2015-04-08 | 2017-02-01 | 中国科学院化学研究所 | 一种2,2’‑二(苯并噻吩)乙烯聚合物及其制备方法与应用 |
| US10109798B2 (en) * | 2015-05-26 | 2018-10-23 | Purdue Research Foundation | Methods and compositions for enhancing processability and charge transport of polymer semiconductors |
| WO2017006765A1 (ja) | 2015-07-07 | 2017-01-12 | 富士フイルム株式会社 | 有機半導体素子、化合物、有機半導体組成物、および、有機半導体膜の製造方法 |
| WO2017006703A1 (ja) * | 2015-07-07 | 2017-01-12 | 富士フイルム株式会社 | 有機半導体素子、化合物、有機半導体組成物、並びに、有機半導体膜及びその製造方法 |
| WO2017038944A1 (ja) * | 2015-09-02 | 2017-03-09 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機薄膜トランジスタの製造方法、有機半導体組成物、有機半導体膜および有機半導体膜の製造方法 |
| KR20160088257A (ko) | 2016-02-05 | 2016-07-25 | 경상대학교산학협력단 | 비대칭 헤테로고리-비닐렌-헤테로고리계 다이케토피롤로피롤 중합체, 이를 채용하고 있는 유기 전자 소자 및 이를 제조하기 위한 단량체 |
| US10741766B2 (en) * | 2016-05-12 | 2020-08-11 | Samsung Electronics Co., Ltd. | Organic semiconductor thin film and method of manufacturing the same and thin film transistor and electronic device |
| US11384197B2 (en) | 2016-05-25 | 2022-07-12 | Clap Co., Ltd. | Semiconductors |
| US11319396B2 (en) | 2016-09-27 | 2022-05-03 | Basf Se | Star-shaped and triblock polymers with enhanced crosslinkability |
| WO2018060015A1 (en) | 2016-09-27 | 2018-04-05 | Basf Se | Star-shaped styrene polymers with enhanced glass transition temperature |
| US12415885B2 (en) * | 2016-10-11 | 2025-09-16 | The Hong Kong University Of Science And Technology | Ternary blend organic solar cells based on one donor polymer and two acceptors |
| WO2019170481A1 (en) | 2018-03-07 | 2019-09-12 | Basf Se | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
| US20200411781A1 (en) | 2018-03-08 | 2020-12-31 | Clap Co., Ltd. | Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material |
| KR102457044B1 (ko) | 2018-06-26 | 2022-10-21 | 주식회사 클랩 | 유전체로서의 비닐에테르계 고분자 |
| CN111045296B (zh) * | 2018-10-12 | 2024-12-27 | 康宁股份有限公司 | 用于有机薄膜晶体管的可uv图案化的聚合物掺混物 |
| JP7151468B2 (ja) * | 2018-12-25 | 2022-10-12 | 東洋インキＳｃホールディングス株式会社 | 蛍光標識剤 |
| EP3933949A1 (en) | 2020-06-30 | 2022-01-05 | Basf Se | Composition comprising an organic semiconducting polymer and a crosslinking agent and organic photodiode thereof |
| WO2024035888A1 (en) * | 2022-08-10 | 2024-02-15 | Kennesaw State University Research And Service Foundation, Inc. | Pyrrole derived compositions and sythesis methods |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005049695A1 (en) * | 2003-10-28 | 2005-06-02 | Ciba Specialty Chemicals Holding Inc. | Novel diketopyrrolopyrrole polymers |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR920002741A (ko) * | 1990-07-20 | 1992-02-28 | 베르너 발데크 | 디케토피롤로피롤을 기재로 하는 전기 발색 조성물 |
| DE59404868D1 (de) * | 1993-07-20 | 1998-02-05 | Ciba Geigy Ag | In der Masse mit Diketopyrrolopyrrolpigmenten gefärbte Polyamide |
| EP0648770B1 (de) * | 1993-10-13 | 2000-05-17 | Ciba SC Holding AG | Pyrrolo[3,4-c]pyrrole |
| US5492564A (en) * | 1994-03-16 | 1996-02-20 | Ciba-Geigy Corporation | Diketopyrrolopyrrole pigment with high chroma |
| DE59507427D1 (de) * | 1994-09-28 | 2000-01-20 | Ciba Sc Holding Ag | Mischkristalle und feste Lösungen von 1,4-Diketopyrrolopyrrolen |
| EP0718697B1 (en) * | 1994-12-22 | 2001-11-21 | Ciba SC Holding AG | Electrophotographic photoreceptor |
| JP3704748B2 (ja) * | 1995-06-23 | 2005-10-12 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子用電子輸送材料およびそれを用いた有機エレクトロルミネッセンス素子 |
| TW341572B (en) * | 1995-09-20 | 1998-10-01 | Ciba Sc Holding Ag | Preparation of mixed crystals and solid solutions of 1,4-diketopyrrolopyrroles |
| DE59704157D1 (de) * | 1996-01-30 | 2001-09-06 | Ciba Sc Holding Ag | Polymerisierbare Diketopyrrolopyrrole und damit hergestellte Polymere |
| WO1998025927A1 (en) * | 1996-12-10 | 1998-06-18 | Ciba Specialty Chemicals Holding Inc. | Liquid crystalline diketopyrrolopyrroles |
| JP4558106B2 (ja) * | 1997-01-27 | 2010-10-06 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 改良された溶解性基を有する可溶性発色団 |
| TWI290164B (en) * | 1999-08-26 | 2007-11-21 | Ciba Sc Holding Ag | DPP-containing conjugated polymers and electroluminescent devices |
| EP1329493A3 (en) * | 1999-09-27 | 2007-05-23 | Ciba SC Holding AG | Electroluminescent devices comprising diketopyrrolopyrroles |
| EP1087005B1 (en) * | 1999-09-27 | 2004-02-25 | Ciba SC Holding AG | Fluorescent diketopyrrolopyrroles |
| EP1101800B1 (en) * | 1999-11-17 | 2003-06-25 | Ciba SC Holding AG | Diketopyrrolopyrrole |
| US6388093B1 (en) * | 2001-01-05 | 2002-05-14 | Sun Chemical Corporation | Syntheses for preparing 1,4-diketopyrrolo [3,4-c]pyrroles |
| US6878505B2 (en) * | 2001-05-28 | 2005-04-12 | Fuji Photo Film Co., Ltd. | Photosensitive composition |
| KR100558750B1 (ko) * | 2001-12-03 | 2006-03-14 | 도요 잉키 세이조 가부시끼가이샤 | 유기 전계발광 소자용 조성물 및 그것을 사용한 유기전계발광 소자 |
| JP2005526152A (ja) * | 2002-02-01 | 2005-09-02 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | ジケトピロロピロールを含む蛍光組成物 |
| JP4093083B2 (ja) * | 2003-03-10 | 2008-05-28 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| WO2004090046A1 (en) * | 2003-04-10 | 2004-10-21 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles |
| JP4911486B2 (ja) | 2005-04-13 | 2012-04-04 | 東洋インキＳｃホールディングス株式会社 | 有機トランジスタ |
| BRPI0713952A2 (pt) | 2006-06-30 | 2012-12-04 | Ciba Holding Inc | polìmeros de dicetopirrolopirrol como semicondutores orgánicos |
| US7910684B2 (en) * | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
| US7932344B2 (en) | 2007-09-06 | 2011-04-26 | Xerox Corporation | Diketopyrrolopyrrole-based polymers |
| WO2009047104A2 (en) | 2007-10-09 | 2009-04-16 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use |
| WO2010049323A1 (en) | 2008-10-31 | 2010-05-06 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| CN107099023B (zh) * | 2008-10-31 | 2019-10-22 | 巴斯夫欧洲公司 | 用于有机场效应晶体管的二酮吡咯并吡咯聚合物 |
| US8624232B2 (en) | 2009-08-28 | 2014-01-07 | Prashant Sonar | Ambipolar polymeric semiconductor materials and organic electronic devices |
| US8946376B2 (en) * | 2010-09-29 | 2015-02-03 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
-
2007
- 2007-06-20 BR BRPI0713952-7A patent/BRPI0713952A2/pt not_active IP Right Cessation
- 2007-06-20 CA CA002655076A patent/CA2655076A1/en not_active Abandoned
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-
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005049695A1 (en) * | 2003-10-28 | 2005-06-02 | Ciba Specialty Chemicals Holding Inc. | Novel diketopyrrolopyrrole polymers |
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| EP2035428A1 (en) | 2009-03-18 |
| JP5374367B2 (ja) | 2013-12-25 |
| CA2655076A1 (en) | 2008-01-03 |
| KR101422054B1 (ko) | 2014-07-23 |
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